There is consensus that experiences gained during immigration have an impact on health status. However, studies comparing health-related outcomes in homogeneous groups of immigrants living in different host countries are rare. In a sample of Jewish immigrants from the Former Soviet Union (FSU) in two different host countries, Germany and Israel, possible predictors of health-related quality of life (HRQoL) and satisfaction with life (SWL) were examined. In total, 359 Jewish immigrants from the FSU living in Germany (n = 180) and Israel (n = 179) completed the questionnaire measuring immigration-related and sociodemographic characteristics. HRQoL was assessed via Short Form Health Survey Version 2 (SF-12v2), and SWL via Satisfaction With Life Scale (SWLS). Hierarchical linear regression models were applied for analyzing immigration-related and sociodemographic predictors of HRQoL and SWL. Participants living in Israel scored higher on HRQoL, and no differences were found concerning SWL ratings. However, no direct influences of the host country were detected by predicting HRQoL and SWL scores. In both subgroups, immigration-related factors such as perceived discrimination or level of integration were found as significant predictors. In the face of different immigration waves in the host countries, Germany and Israel, the results display similarities rather than differences between the groups concerning the sociodemographic and immigration-related predictors on HRQoL and SWL. The findings using cross-cultural analysis level underscore the need of much more detailed future research on this issue.